Bromine → 5,7-Difluorobenzo[d]thiazol-2-amine

HRID 30885

Reaktionsgleichung

Reaktionsgleichung von HRID 30885
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([F:8])[CH:7]=1.BrBr>ClCCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]2[S:11][C:10]([NH2:12])=[N:9][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 2783293(3,5-Difluorophenyl)thiourea

Produkt 1

HCID 150505645,7-Difluorobenzo[d]thiazol-2-amineAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a suspension of N-(3,5-difluorophenyl) thiourea (3.40 g, 18.07 mmol) in DCE (95 mL) was added a solution of bromine in DCE (5 mL) below 30° C. The mixture was heated at reflux for 2.5 h, then cooled to 10° C., and the precipitate formed was collected by filtration and washed with DCE. The solid was stirred with water (200 mL), basified by treatment with conc. ammonium hydroxide, filtered, and dried in a vacuum oven to afford 5,7-difluoro-1,3-benzothiazol-2-amine (3.05 g, 90%). ret. time 2.18; m/z 187.1 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 6.92 (m, 1H), 7.00 (m, 2H), 7.92 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 h
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with DCE
  6. filtrationfiltered
  7. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-e05c5f3294924d8ab7c23eb1f3297773
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423156B2

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